I. Aleksanyan, L. Hambardzumyan
Dec 1, 2013
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Journal
Russian Journal of Organic Chemistry
Abstract
Many quinoline derivatives are known as efficient fluorophores [1] and are widely used in biochemistry and medicine for studying various biological systems. Nowadays, much attention is given to DNA fluorophores based on fused aromatic systems containing two and more rings (preferably fiveor six-membered) and at least one heteroatom. Nevertheless, search for new more sensitive and selective compounds remains important [2]. Quinoline derivatives, in particular aminoquinolines, are also promising as potential antioxidants and radioprotectors [3]. In view of the above stated, in the present work we studied reactions of 2-chloro-4-methylquinolines with 2and 4-aminobenzoic acids and ethyl 4-aminobenzoate to obtain new quinoline derivatives. By heating 2-chloro-4-methylquinolines Ia–Ic with 2-aminobenzoic acid or ethyl 4-aminobenzoate at a ratio of 1 : 1.1 in ethanol in the presence of HCl for 9–15 h we synthesized the corresponding 2-(2-carboxyphenylamino)and 2-(4-ethoxycarbonylphenylamino)-4-methylquinolines IIa–IIc and IIIa–IIIc, respectively, in high yields (Scheme 1). Alkaline hydrolysis of esters IIIa–IIIc